cis-(+)-Disparlure

Base Information

• Chemical Name: cis-(+)-Disparlure
• CAS No.: 54910-51-9
• Molecular Formula: C19H38 O
• Molecular Weight: 282.51
• Hs Code.: 2910900090
• European Community (EC) Number: 259-390-8
• UNII: A5ZD42XF7G
• DSSTox Substance ID: DTXSID8075041
• Nikkaji Number: J9.364E
• Wikipedia: Disparlure
• Wikidata: Q27273667
• Metabolomics Workbench ID: 5648
• Mol file: 54910-51-9.mol

Synonyms:cis-(+)-Disparlure;54910-51-9;(+)-DISPARLURE;(2S,3R)-2-decyl-3-(5-methylhexyl)oxirane;2-methyl-7R,8S-Epoxy-octadecane;Disparlure (2S-cis)-;UNII-A5ZD42XF7G;A5ZD42XF7G;EINECS 259-390-8;(2S-cis)-7,8-Epoxy-2-methyloctadecane;Oxirane, 2-decyl-3-(5-methylhexyl)-, (2S,3R)-;DISPARLURE [MI];DISPARLURE,(+)-;(2S-CIS)-DISPARLURE;(7R,8S)-DISPARLURE;SCHEMBL432739;DISPARLURE, CIS-(+)-;DTXSID8075041;CHEBI:179292;LMFA12000282;MFCD06799016;cis-(7S,8R)-(+)-epoxy-2-methyloctadecane;Oxirane, 2-decyl-3-(5-methylhexyl)-, (2S-cis)-;Q27273667

Chemical Property of cis-(+)-Disparlure

Chemical Property:

• Vapor Pressure: 0.000168mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 146-148 °C0.25 mm Hg(lit.)
• Flash Point: 125 °F
• PSA: 12.53000
• Density: 0.828 g/mL at 25 °C(lit.)
• LogP: 6.50100
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 282.292265831
• Heavy Atom Count: 20
• Complexity: 212

Purity/Quality:

99.3% ^*data from raw suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC1C(O1)CCCCC(C)C
• Isomeric SMILES: CCCCCCCCCC[C@H]1[C@H](O1)CCCCC(C)C
• General Description: (+)-Disparlure, also known as (7R,8S)-(+)-Disparlure or cis-(+)-Disparlure, is a sex pheromone component of the gypsy moth (*Lymantria dispar*). It features a *cis*-epoxide functional group and exhibits strong attraction to male gypsy moths. The enantioselective synthesis of (+)-disparlure has been achieved through various methods, including asymmetric dihydroxylation, palladium-catalyzed domino reactions, and enantioselective iodolactonization. Studies on its binding with pheromone-binding proteins (PBPs) reveal distinct interactions, with PBP2 showing a stronger affinity for (+)-disparlure compared to its antipode. The pheromone's stereochemistry and binding behavior are crucial for its biological activity in gypsy moth communication.

Technology Process of cis-(+)-Disparlure

There total 185 articles about cis-(+)-Disparlure which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

cis-2-Methyl-7-octadecen (35354-39-3) → disparlure (29804-22-6,35898-62-5,42991-03-7,54910-51-9,54910-52-0,54910-53-1,54910-54-2,57457-72-4,65634-82-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1055/s-1983-30302

Reference yield:

trans-7,8-epoxy-2-methyloctadecane (51050-50-1) → disparlure (29804-22-6,35898-62-5,42991-03-7,54910-51-9,54910-52-0,54910-53-1,54910-54-2,57457-72-4,65634-82-4) + trans-7,8-epoxy-2-methyloctadecane (42991-03-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; Title compound not separated from byproducts;

DOI:10.1016/0022-328X(85)87361-7

Reference yield:

2-methyloctadec-7-yne (35354-38-2) → disparlure (29804-22-6,35898-62-5,42991-03-7,54910-51-9,54910-52-0,54910-53-1,54910-54-2,57457-72-4,65634-82-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Lindlar / ethanol / Ambient temperature

2: m-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

With hydrogen; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In ethanol; dichloromethane;

upstream raw materials:

cis-2-Methyl-7-octadecen

triphenyl-1-(4-methyl)-pentyl-phosphorane

cis-2,3-epoxytridecan-1-al

(-)-2-methyl-(5Z,7R,8S)-epoxyoctadec-5-ene

Downstream raw materials:

2-Methyloctadecan-7-one

2-methyloctadecan-8-one